A general, polymer-supported acid catalyzed hetero-Michael addition

Synlett

Volumn , Issue 7, 2003, Pages 1070-1072

  Wabnitz, Tobias C ^a   Yu, Jin Quan ^a   Spencer, Jonathan B ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Enones; hetero Michael additions; Heterogeneous catalysis; Nafion ; Polymer support

Indexed keywords

KETONE DERIVATIVE; NITROGEN; OXYGEN; POLYMER; SULFONIC ACID DERIVATIVE; SULFUR;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; FLUORINATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0038575857     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39292     Document Type: Article

References (30)

1. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815.
2. Recent examples: (a) Nagayama, S.; Kobayashi, S. Angew. Chem. Int. Ed. 2000, 39, 567. (b) Kobayashi, S.; Nagayama, S. Synlett 1997, 653. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
3. Recent examples: (a) Nagayama, S.; Kobayashi, S. Angew. Chem. Int. Ed. 2000, 39, 567. (b) Kobayashi, S.; Nagayama, S. Synlett 1997, 653. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
4. Recent examples: (a) Nagayama, S.; Kobayashi, S. Angew. Chem. Int. Ed. 2000, 39, 567. (b) Kobayashi, S.; Nagayama, S. Synlett 1997, 653. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
5. Villemin, D.; Martin, B. J. Chem. Res. 1994, 146.
6. Sercheli R., Ferreira A. L. B., Guerreiro M. C., Vargas R. M., Sheldon R. A., Schuchardt U.; Tetrahedron Lett.; 1997, 38: 1325.
7. Recent developments: (a) Choudary, B. M.; Kantam, M. L.; Reddy, C. R. V.; Rao, K. K.; Figueras, F. J. Mol. Cat. A 1999, 146, 279. (b) Zahouily, M.; Abrouki, Y.; Rayadh, A.; Sebti, S.; Dhimane, H.; David, M. Tetrahedron Lett. 2003, 44, 2463.
8. Recent developments: (a) Choudary, B. M.; Kantam, M. L.; Reddy, C. R. V.; Rao, K. K.; Figueras, F. J. Mol. Cat. A 1999, 146, 279. (b) Zahouily, M.; Abrouki, Y.; Rayadh, A.; Sebti, S.; Dhimane, H.; David, M. Tetrahedron Lett. 2003, 44, 2463.
9. (a) Pelletier, S. W.; Venkov, A. P.; Finer-Moore, J.; Mody, N. Tetrahedron Lett. 1980, 21, 809.
10. (b) Cornelis, A.; Laszlo, P. Synlett 1994, 155.
11. (c) Shaikh, N. S.; Deshpande, V. H.; Bedekar, A. V. Tetrahedron 2001, 57, 9045.
12. (d) Sundararajan, G.; Prabagaran, N. Org. Lett. 2001, 3, 389.
13. (e) Bartoli, G.; Bosco, M.; Marcantoni, E.; Petrini, M.; Sambri, L.; Torregiani, E. J. Org. Chem. 2001, 66, 9052.
14. (f) Lorette, N. B. J. Org. Chem. 1958, 23, 937.
15. (g) Kabashima, H.; Katou, T.; Hattori, H. Appl. Cat. A 2001, 214, 121.
16. Wabnitz, T. C.; Spencer, J. B. Org. Lett. 2003, 5, in press.
17. (a) Olah, G. A.; Iyer, P. S.; Prakash, G. K. S. Synthesis 1986, 513.
18. (b) Harmer, M. A.; Sun, Q. Appl. Cat. A 2001, 221, 45.
19. (a) Török, B.; Kiricsi, I.; Molnar, A.; Olah, G. A. J. Cat. 2000, 193, 132.
20. (b) Heidekum, A.; Harmer, M. A.; Hoelderich, W. F. J. Cat. 1999, 181, 217.
21. -1) at room temperature. The reaction was monitored by TLC and the product was isolated by preparative TLC after filtering off the catalyst.
22. Hayashi, Y.; Nishimura, K. Chem. Lett. 2002, 296.
23. 9b
24. (a) Gaunt, M. J.; Spencer, J. B. Org. Lett. 2001, 3, 25.
25. (b) Wabnitz, T. C.; Spencer, J. B. Tetrahedron Lett. 2002, 43, 3891.
26. (c) Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319.
27. 7).
28. Catalyst regeneration: Spent Nafion® SAC-13 was stirred over 6 N HCl (0.5 mL) overnight. After filtration, the catalyst was dried in vacuo for 20 h and reused.
29. +). Mp: 55-57°C.
30. Ishihara, K.; Hasegawa, A.; Yamamoto, H. Angew. Chem. Int. Ed. 2001, 40, 4077.